Abstract
This paper reports new applications of the cathodically promoted addition of nitro compounds to the biomass‐derived enone, levoglucosenone. A series of 2‐substituted 1,3‐dinitropropanes were found to undergo addition to levoglucosenone with generation of a tricyclic product containing a fused cyclohexane system. The reaction yields are good to excellent and are catalyzed by base (superoxide) generated electrochemically. Derivatives were prepared from 1,3‐dinitropropanes with the following 2‐substituents: 2‐thienyl, 2‐furyl, N‐methyl‐2‐pyrryl, phenyl, 9‐anthryl, and ferrocenyl. The structure of the derivative from 2‐ferrocenyl‐1,3‐dinitropropane was established by X‐ray crystallography, thus confirming the NMR‐based stereochemical assignments of all of the other products. © 2000 The Electrochemical Society. All rights reserved.